Dehydrogenation of anhydrous methanol at room temperature by o-aminophenol-based photocatalysts

Nature Communications

Volumn 7, Issue , 2016, Pages

  Wakizaka, Masanori ^a   Matsumoto, Takeshi ^a   Tanaka, Ryota ^a   Chang, Ho Chol ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPHENOL; FORMALDEHYDE; HYDROGEN; IRON COMPLEX; METHANOL; PHOTOSENSITIZING AGENT; SCAVENGER;

CATALYST; CHEMICAL COMPOUND; CHEMICAL REACTION; DEHYDRATION; FORMALDEHYDE; HETEROGENEITY; METHANOL; PHENOLIC COMPOUND; PHOTOCHEMISTRY; TEMPERATURE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEHYDROGENATION; ELECTRON TRANSPORT; HIGH TEMPERATURE; HYDROGEN EVOLUTION; INFRARED SPECTROSCOPY; PHOTOCATALYSIS; PHOTOCATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS; ROOM TEMPERATURE; ULTRAVIOLET SPECTROSCOPY;

EID: 84979742724     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms12333     Document Type: Article

References (68)

1. Armaroli, N., Balzani, V. The future of energy supply: challenges and opportunities. Angew. Chem. Int. Ed. 46, 52-66 (2007).
2. Du, P., Eisenberg, R. Catalysts made of earth-abundant elements (Co, Ni, Fe) for water splitting: recent progress and future challenges. Energy Environ. Sci. 5, 6012-6021 (2012).
3. Esswein, A. J., Nocera, D. G. Hydrogen production by molecular photocatalysis. Chem. Rev. 107, 4022-4047 (2007).
4. Kubas, G. J. Fundamentals of H2 binding and reactivity on transition metals underlying hydrogenase function and H2 production and storage. Chem. Rev. 107, 4152-4205 (2007).
5. Lewis, N. S., Nocera, D. G. Powering the planet: chemical challenges in solar energy utilization. Proc. Natl Acad. Sci. USA 103, 15729-15735 (2006).
6. Reece, S. Y. et al. Wireless solar water splitting using silicon-based semiconductors and earth-abundant catalysts. Science 334, 645-648 (2011).
7. Eberle, U., Felderhoff, M., Schüth, F. Chemical and physical solutions for hydrogen storage. Angew. Chem. Int. Ed. 48, 6608-6630 (2009).
8. Schlapbach, L., Zuttel, A. Hydrogen-storage materials for mobile applications. Nature 414, 353-358 (2001).
9. Suh, M. P., Park, H. J., Prasad, T. K., Lim, D.-W. Hydrogen storage in metal-organic frameworks. Chem. Rev. 112, 782-835 (2011).
10. Penã, M. A., Gómez, J. P., Fierro, J. L. G. New catalytic routes for syngas and hydrogen production. Appl. Catal. A Gen. 144, 7-57 (1996).
11. Haw, J. F., Song, W., Marcus, D. M., Nicholas, J. B. The mechanism of methanol to hydrocarbon catalysis. Acc. Chem. Res. 36, 317-326 (2003).
12. Navarro, R. M., Penã, M. A., Fierro, J. L. G. Hydrogen production reactions from carbon feedstocks: fossil fuels and biomass. Chem. Rev. 107, 3952-3991 (2007).
13. Holladay, J. D., Hu, J., King, D. L., Wang, Y. An overview of hydrogen production technologies. Catal. Today 139, 244-260 (2009).
14. Rowsell, J. L. C., Yaghi, O. M. Strategies for hydrogen storage in metal-organic frameworks. Angew. Chem. Int. Ed. 44, 4670-4679 (2005).
15. Rosi, N. L. et al. Hydrogen storage in microporous metal-organic frameworks. Science 300, 1127-1129 (2003).
16. Tiwari, J. N., Tiwari, R. N., Singh, G., Kim, K. S. Recent progress in the development of anode and cathode catalysts for direct methanol fuel cells. Nano Energy 2, 553-578 (2013).
17. Biniwale, R. B., Rayalu, S., Devotta, S., Ichikawa, M. Chemical hydrides: a solution to high capacity hydrogen storage and supply. Int. J. Hydrogen Energy 33, 360-365 (2008).
18. Neburchilov, V., Martin, J., Wang, H., Zhang, J. A review of polymer electrolyte membranes for direct methanol fuel cells. J. Power Sources 169, 221-238 (2007).
19. Liu, H. et al. A review of anode catalysis in the direct methanol fuel cell. J. Power Sources 155, 95-110 (2006).
20. Sá, S., Silva, H., Brandaõ, L., Sousa, J. M., Mendes, A. Catalysts for methanol steam reforming-a review. Appl. Catal. B Environ. 99, 43-57 (2010).
21. Nielsen, M. et al. Low-temperature aqueous-phase methanol dehydrogenation to hydrogen and carbon dioxide. Nature 495, 85-89 (2013).
22. Alberico, E. et al. Selective hydrogen production from methanol with a defined iron pincer catalyst under mild conditions. Angew. Chem. Int. Ed. 52, 14162-14166 (2013).
23. Rodréguez-Lugo, R. E. et al. A homogeneous transition metal complex for clean hydrogen production from methanol-water mixtures. Nat. Chem. 5, 342-347 (2013).
24. Johnson, T. C., Morris, D. J., Wills, M. Hydrogen generation from formic acid and alcohols using homogeneous catalysts. Chem. Soc. Rev. 39, 81-88 (2010).
25. Itagaki, H., Saito, Y., Shinoda, S. Transition metal homogeneous catalysis for liquid phase dehydrogenation of methanol. J. Mol. Catal. 41, 209-220 (1987).
26. Hu, P., Diskin-Posner, Y., Ben-David, Y., Milstein, D. Reusable homogeneous catalytic system for hydrogen production from methanol and water. ACS Catal. 4, 2649-2652 (2014).
27. Trincado, M., Banerjee, D., Grützmacher, H. Molecular catalysts for hydrogen production from alcohols. Energy Environ. Sci. 7, 2464-2503 (2014).
28. Alberico, E., Nielsen, M. Towards a methanol economy based on homogeneous catalysis: methanol to H2 and CO2 to methanol. Chem. Commun. 51, 6714-6725 (2015).
29. Campos, J., Sharninghausen, L. S., Manas, M. G., Crabtree, R. H. Methanol dehydrogenation by iridium N-heterocyclic carbene complexes. Inorg. Chem. 54, 5079-5084 (2015).
30. Shinoda, S., Itagaki, H., Saito, Y. Dehydrogenation of methanol in the liquid phase with a homogeneous ruthenium complex catalyst. J. Chem. Soc. Chem. Commun. 860-861 (1985).
31. Itagaki, H., Shinoda, S., Saito, Y. Liquid-Phase dehydrogenation of methanol with homogeneous ruthenium complex catalysts. Bull. Chem. Soc. Jpn. 61, 2291-2294 (1988).
32. Fujii, T., Saito, Y. Catalytic dehydrogenation of methanol with ruthenium complexes. J. Mol. Catal. 67, 185-190 (1991).
33. Yang, L.-C., Ishida, T., Yamakawa, T., Shinoda, S. Mechanistic study on dehydrogenation of methanol with [RuCl2(PR3)3]-type catalyst in homogeneous solutions. J. Mol. Catal. A Chem. 108, 87-93 (1996).
34. Delgado-Lieta, E., Luke, M. A., Jones, R. F., Cole-Hamilton, D. J. The photochemical decomposition of alcohols catalysed by tri(isopropyl) phosphine complexes of rhodium(I). Polyhedron 1, 839-840 (1982).
35. Morton, D., Cole-Hamilton, D. J. Molecular hydrogen complexes in catalysis: highly efficient hydrogen production from alcoholic substrates catalysed by ruthenium complexes. J. Chem. Soc. Chem. Commun. 1154-1156 (1988).
36. Takahashi, T., Shinoda, S., Saito, Y. The mechanisms of photocatalytic dehydrogenation of methanol in the liquid phase with cis-[Rh2Cl2(CO)2(dpm)2] complex catalyst. J. Mol. Catal. 31, 301-309 (1985).
37. Yamamoto, H., Shinoda, S., Saito, Y. Photocatalytic dehydrogenation of methanol in the liquid phase with cis-Rh2Cl2(CO)2(dpm)2 and Pd2Cl2(dpm)2 complex catalysts. J. Mol. Catal. 30, 259-266 (1985).
38. Nomura, K., Saito, Y., Shinoda, S. Photoenhanced catalytic dehydrogenation of methanol with tin(II)-coordinated iridium complexes. J. Mol. Catal. 50, 303-313 (1989).
39. Makita, K., Nomura, K., Saito, Y. Photocatalytic dehydrogenation of methanol using [IrH(SnCl3)5]3-complex. J. Mol. Catal. 89, 143-149 (1994).
40. Reuss, G., Disteldorf, W., Grundler, O., Hilt, A. Ullmann's Encyclopedia of Industrial Chemistry (VCH, 1985).
41. Matsumoto, T. et al. Nonprecious-metal-assisted photochemical hydrogen production from ortho-phenylenediamine. J. Am. Chem. Soc. 135, 8646-8654 (2013).
42. Bittner, M. M., Lindeman, S. V., Fiedler, A. T. A synthetic model of the putative Fe(II)-iminobenzosemiquinonate intermediate in the catalytic cycle of o-aminophenol dioxygenases. J. Am. Chem. Soc. 134, 5460-5463 (2012).
43. Bittner, M. M., Kraus, D., Lindeman, S. V., Popescu, C. V., Fiedler, A. T. Synthetic, spectroscopic, and DFT studies of iron complexes with iminobenzo(semi)quinone ligands: Implications for o-aminophenol dioxygenases. Chem. Eur. J. 19, 9686-9698 (2013).
44. Chakraborty, B., Paine, T. K. Aromatic ring cleavage of 2-amino-4-tertbutylphenol by a nonheme iron(II) complex: functional model of 2-aminophenol dioxygenases. Angew. Chem. Int. Ed. 52, 920-924 (2013).
45. Chakraborty, B., Bhunya, S., Paul, A., Paine, T. K. Reactivity of biomimetic iron(II)-2-aminophenolate complexes toward dioxygen: mechanistic investigations on the oxidative C-C bond cleavage of substituted 2-aminophenols. Inorg. Chem. 53, 4899-4912 (2014).
46. Banerjee, S., Halder, P., Paine, T. K. Probing the reactivity of redox-active 2-aminophenolates on iron complexes of a carbanionic N3C donor ligand. Z. Anorg. Allg. Chem. 640, 1168-1176 (2014).
47. Capello, M. C. et al. Fast nonradiative decay in o-aminophenol. J. Phys. Chem. A 118, 2056-2062 (2014).
48. Becker, R., Wei-, J., Winter, M., Merz, K., Fischer, R. A. New heterometallic copper zinc alkoxides: synthesis, structure properties and pyrolysis to Cu/ZnO composites. J. Organomet. Chem. 630, 253-262 (2001).
49. Reynolds, M. et al. 4-Nitrocatechol as a probe of a Mn(II)-dependent extradiol-cleaving catechol dioxygenase (MndD): comparison with relevant Fe(II) and Mn(II) model complexes. J. Biol. Inorg. Chem. 8, 263-272 (2003).
50. Bordwell, F. G., Algrim, D. J. Acidities of anilines in dimethyl sulfoxide solution. J. Am. Chem. Soc. 110, 2964-2968 (1988).
51. Bordwell, F. G., McCallum, R. J., Olmstead, W. N. Acidities and hydrogen bonding of phenols in dimethyl sulfoxide. J. Org. Chem. 49, 1424-1427 (1984).
52. Cairns, C., Nelson, S. M., Drew, M. G. B. Iron(II) complexes of a potentially quinquedentate macrocyclic ligand having an 'N3S2' donor set and the crystal and molecular structures of a high-spin (S=2) complex and a low-spin (S=0) complex. J. Chem. Soc. Dalton Trans. 1965-1972 (1981).
53. Jonas, R. T., Stack, T. D. P. C-H bond activation by a ferric methoxide complex: a model for the rate-determining step in the mechanism of lipoxygenase. J. Am. Chem. Soc. 119, 8566-8567 (1997).
54. Büttner, T. et al. A stable aminyl radical metal complex. Science 307, 235-238 (2005).
55. Zielonka, J., Marcinek, A., Adamus, J., Gȩbicki, J. Direct observation of NADH radical cation generated in reactions with one-electron oxidants. J. Phys. Chem. A 107, 9860-9864 (2003).
56. Matsubara, Y. et al. Development of an efficient and durable photocatalytic system for hydride reduction of an NAD(P)\+ model compound using a ruthenium(II) complex based on mechanistic studies. J. Am. Chem. Soc. 132, 10547-10552 (2010).
57. Campano, D. D., Kantrowitz, E. R., Hoffman, M. Z., Weinberg, M. S. Generation of radicals in the charge-transfer photochemistry of coordination complexes of colbalt(III) in aqueous solution. J. Phys. Chem. 78, 686-691 (1974).
58. Roberts, G. M. et al. Unraveling ultrafast dynamics in photoexcited aniline. J. Am. Chem. Soc. 134, 12578-12589 (2012).
59. Montero, R. et al. Ultrafast dynamics of aniline in the 294-234 nm excitation range: the role of the πσ∗ state. J. Chem. Phys. 135, 054308 (2011).
60. 1πσ∗ state mediated photodissociation of aniline. J. Chem. Phys. 132, 214307-214312 (2010).
61. Ujike, K., Kudoh, S., Nakata, M. First detection of 7,8-diazabicyclo[4.2.0]octa-1,3,5-triene produced from 3,5-cyclohexadiene-1,2-diimine in an argon matrix. Chem. Phys. Lett. 396, 288-292 (2004).
62. Ujike, K., Akai, N., Kudoh, S., Nakata, M. Photoisomerization and photocyclization of 3,5-cyclohexadiene-1,2-diimine and its methyl-substituted derivatives in low-temperature argon matrices. J. Mol. Struct. 735-736, 335-342 (2005).
63. Horváth, T., Kaizer, J., Speier, G. Functional phenoxazinone synthase models: kinetic studies on the copper-catalysed oxygenation of 2-aminophenol. J. Mol. Catal. A Chem. 215, 9-15 (2004).
64. Sritharathikhun, P., Oshima, M., Motomizu, S. On-line collection/concentration of trace amounts of formaldehyde in air with chromatomembrane cell and its sensitive determination by flow injection technique coupled with spectrophotometric and fluorometric detection. Talanta 67, 1014-1022 (2005).
65. Nash, T. Colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J. 55, 416-421 (1953).
66. Hantzsch, A. Condensationsprodukte aus Aldehydammoniak und ketonartigen Verbindungen. Ber. Dtsch. Chem. Ges. 14, 1637-1638 (1881).
67. Christian, G. D. Analytical Chemistry 6th edn (John Wiley & Sons. Inc., 2004).
68. Miller, J. N., Miller, J. C. Statistics And Chemometrics For Analytical Chemistry 4th edn (Pearson Education Limited, 2000).